If you have ever been attracted to a friend, perhaps you have felt that asking her on a date is venturing into dangerous, friendship-endangering territory. But the benefits of dating a friend can be well worth your effort. According to the website Romancetips, "In dating a friend, you aren't starting over but adding a new dimension to a relationship that you already value."
Timing
You won't be able to control your friend's response when you ask him out, but you should control as much of the situation as you can. "Getting your timing right is one of the single most important factors," according to the website Topdatingtips. For example, if he is interested in someone else you might want to wait until that plays itself out before you ask him out. Look for opportunities where you can be alone. He probably will pick up on your subtle advances, which will prepare him for when you finally do ask him out.
Clarify Expectations
Make sure that your motives are clear to your friend. For example, women often exhibit similar behavior when they are interested in a guy and when they are comfortable around a guy friend, according to the website lovetoknow. Make sure your friend understands that you are asking her on a date. Plan something that you and she do not already do together, but make sure it is something that allows you both to be comfortable. For example, if you usually go to the movies, go bowling instead.
Keep It Casual
When you ask out a friend, you want him to feel comfortable and pressure-free. Your goal is to maintain a good, healthy friendship whether or not he accepts your offer. Be yourself. The actual date does not have to be extravagant, either. If you are interested in him but are concerned about coming off as too forward, one option is to tell him that you have an extra ticket to a show and would like to know if he would like to go with you. This avoids putting him on the spot.
Be Prepared
Be prepared for different reactions from your friend. If your friend says yes, you should already have in mind what kind of activity you would like to do. This demonstrates to her that you have put time and effort into asking her, and she will appreciate that effort. If she says she needs time to think about it, she probably really does. Give her the time and space that she might need to consider this novel idea of dating you.
Dealing with Rejection
If your friend rejects your invitation, just remind yourself that it is not the end of the world. Have a backup plan that maintains your friendship. For example, just suggest doing something that you already do together. Don't make a big deal about it, especially in his presence. As your friend, he will respect you for your efforts and might even appreciate your friendship more than he previously did.
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